Who was Caravaggio's black-winged deity of desire? The insights that masterwork uncovers about the rogue artist

The youthful lad cries out as his skull is firmly gripped, a massive thumb pressing into his cheek as his father's mighty hand grasps him by the throat. This moment from Abraham's Sacrifice appears in the Florentine museum, creating distress through the artist's chilling portrayal of the tormented youth from the biblical narrative. The painting seems as if the patriarch, instructed by the Divine to sacrifice his offspring, could break his neck with a single twist. However Abraham's chosen method involves the silvery steel knife he holds in his other hand, prepared to cut the boy's neck. A certain aspect remains – whoever modeled as the sacrifice for this breathtaking piece demonstrated extraordinary expressive skill. There exists not just dread, shock and begging in his shadowed gaze but also profound sorrow that a protector could abandon him so utterly.

He took a familiar biblical tale and transformed it so fresh and visceral that its terrors appeared to happen right in front of the viewer

Standing in front of the painting, observers identify this as a real countenance, an accurate depiction of a young model, because the same boy – identifiable by his tousled hair and nearly dark pupils – features in several other works by Caravaggio. In each instance, that highly emotional face commands the scene. In Youth With a Ram, he peers mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a toughness learned on Rome's streets, his dark plumed appendages demonic, a naked adolescent running riot in a affluent residence.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most discomfiting artworks ever painted. Observers feel completely unsettled gazing at it. Cupid, whose arrows inspire people with frequently painful desire, is shown as a very tangible, vividly illuminated unclothed figure, standing over overturned items that include musical instruments, a musical score, plate armour and an architect's T-square. This pile of possessions echoes, deliberately, the mathematical and architectural gear strewn across the floor in Albrecht Dürer's print Melancholy – except here, the gloomy disorder is created by this smirking deity and the mayhem he can unleash.

"Love sees not with the eyes, but with the mind, / And thus is winged Cupid painted sightless," wrote Shakespeare, just before this work was created around 1601. But the painter's god is not unseeing. He gazes straight at the observer. That face – sardonic and rosy-faced, staring with bold confidence as he poses unclothed – is the same one that shrieks in fear in The Sacrifice of Isaac.

As the Italian master painted his three images of the same distinctive-appearing youth in Rome at the dawn of the seventeenth century, he was the highly celebrated religious painter in a metropolis enflamed by Catholic renewal. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could adopt a biblical narrative that had been depicted numerous times previously and render it so new, so raw and visceral that the horror seemed to be happening directly before you.

Yet there existed another side to the artist, evident as soon as he arrived in the capital in the cold season that ended the sixteenth century, as a painter in his early twenties with no mentor or supporter in the city, only skill and audacity. Most of the works with which he caught the holy metropolis's attention were anything but devout. What could be the absolute first resides in the UK's art museum. A youth opens his crimson lips in a scream of pain: while reaching out his dirty fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid squalor: observers can discern the painter's dismal chamber mirrored in the cloudy liquid of the glass container.

The boy sports a pink blossom in his coiffure – a emblem of the sex trade in Renaissance painting. Northern Italian painters such as Tiziano and Palma Vecchio depicted prostitutes holding blooms and, in a painting destroyed in the second world war but documented through images, Caravaggio represented a renowned woman courtesan, holding a posy to her chest. The message of all these floral signifiers is clear: sex for sale.

What are we to interpret of the artist's erotic portrayals of youths – and of one adolescent in specific? It is a question that has divided his interpreters ever since he achieved widespread recognition in the twentieth century. The complex historical reality is that the painter was neither the queer icon that, for instance, Derek Jarman presented on film in his 1986 film about the artist, nor so completely pious that, as certain art scholars unbelievably claim, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial works do make explicit sexual suggestions, or including propositions. It's as if Caravaggio, then a penniless youthful creator, aligned with the city's prostitutes, selling himself to live. In the Uffizi, with this idea in mind, viewers might turn to an additional early work, the 1596 masterwork Bacchus, in which the god of alcohol stares coolly at you as he starts to undo the black ribbon of his robe.

A few annums after Bacchus, what could have motivated the artist to paint Victorious Cupid for the art collector the nobleman, when he was at last becoming almost respectable with prestigious ecclesiastical projects? This unholy non-Christian deity revives the erotic challenges of his early works but in a increasingly intense, unsettling way. Half a century later, its secret seemed obvious: it was a representation of the painter's lover. A British visitor saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this adolescent was Francesco.

The painter had been dead for about 40 annums when this story was documented.

Desiree Adams
Desiree Adams

An avid skier and travel writer with a passion for exploring winter sports destinations across Europe and sharing practical tips.